1163128-59-3

Basic information

• Product Name: ethyl (3R,4R,5S)-5-azido-4-[(tert-butoxycarbonyl)amino]-3-(1-ethylpropoxy)cyclohex-1-ene-1-carboxylate
• Synonyms: ethyl (3R,4R,5S)-5-azido-4-[(tert-butoxycarbonyl)amino]-3-(1-ethylpropoxy)cyclohex-1-ene-1-carboxylate
• CAS NO: 1163128-59-3
• Molecular Weight: 396.487
• Mol File: 1163128-59-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: ethyl (3R,4R,5S)-5-azido-4-[(tert-butoxycarbonyl)amino]-3-(1-ethylpropoxy)cyclohex-1-ene-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl (3R,4R,5S)-5-azido-4-[(tert-butoxycarbonyl)amino]-3-(1-ethylpropoxy)cyclohex-1-ene-1-carboxylate(1163128-59-3)
• EPA Substance Registry System: ethyl (3R,4R,5S)-5-azido-4-[(tert-butoxycarbonyl)amino]-3-(1-ethylpropoxy)cyclohex-1-ene-1-carboxylate(1163128-59-3)

Safety Data

• Hazardous Substances Data: 1163128-59-3(Hazardous Substances Data)

Upstream product

• 204255-02-7 ethyl-(1R,5R,6R)-5-(pentan-3-yloxy)-7-azabicyclo[4.1.0]hept-3-ene-3-carboxylate 
• 204254-98-8 ethyl-(3R,4S,5R)-5-azido-4-hydroxy-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate 
• 204254-96-6 (1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 204255-04-9 ethyl-(3R,4R,5S)-4-amino-5-azido-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate 
• 1401454-88-3 ethyl (3R,4S,5R)-4-(tert-butoxycarbonylamino)-3-(1-ethylpropoxy)-5-(methanesulfonyloxy)cyclohex-1-ene-1-carboxylate 
• 1401454-87-2 ethyl (1S,5R,6S)-7-(tert-butoxycarbonyl)-5-(methanesulfonyloxy)-7-azabicyclo[4.1.0]hept-2-ene-3-carboxylate 
• 1401454-86-1 tert-butyl (2S,3S)-2-ethenyl-3-{(1R)-3-(ethoxycarbonyl)-1-[(methylsulfonyl)oxy]but-3-en-1-yl}aziridine-1-carboxylate 
• 584-02-1 2-pentanol 
• 1163128-58-2 C₁₄H₂₀N₄O₄ 

Downstream Products

• 204255-06-1 oseltamivir 
• 204255-11-8 oseltamivir phosphate 
• 196618-13-0 oseltamivir 
• 204255-04-9 ethyl-(3R,4R,5S)-4-amino-5-azido-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate 
• 1364932-19-3 (3R,4R,5S)-5-(acetylamino)-4-amino-3-(pentan-3-yloxy) cyclohex-1-ene-1-carboxylic acid 

Relevant articles and documents

Synthesis and characterization of potential pharmacopeial impurities of oseltamivir: An antiviral drug

Impurities of oseltamivir phosphate were synthesized from chiral epoxide (1) in a simpler and much feasible synthetic approach in seven steps accounting to 8.2 % overall yield. The nucleophilic addition of N3 (highly regioselective and stereoselective) in

METHOD OF FORMING OSELTAMIVIR AND DERIVATIVES THEREOF

A process is provided for the synthesis of 4,5-diamino cyclohexene carboxylate ester (1): or a pharmaceutically acceptable salt thereof. R1 - R3 are a silyl-, an aliphatic, alicyclic, aromatic, arylaliphatic, or an arylalicyclic group. R4, R11 and R12 are H, a silyl-group, an aliphatic, alicyclic, aromatic, arylaliphatic, or an arylalicyclic group. 3,4-Dihydropyran compound (9): with R5 and R6 being suitable protecting groups, is reacted to form aldehyde (4): which is oxidized and converted to N-substituted carbamate (3): with R7 being a suitable protecting group. (3) is, via oxazolinidone (13): converted to azido carboxylate ester (2): and then to 4,5-diamino cyclohexene carboxylate ester (1).